3-Acetoxymethyl-7-(5-cyanomethyl-1H-benzoimidazol-2-ylamino)-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester

ID: ALA13554

Chembl Id: CHEMBL13554

PubChem CID: 14891884

Max Phase: Preclinical

Molecular Formula: C32H27N5O5S

Molecular Weight: 593.67

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(=O)OCC1=C(C(=O)OC(c2ccccc2)c2ccccc2)N2C(=O)[C@@H](Nc3nc4cc(CC#N)ccc4[nH]3)C2SC1

Standard InChI:  InChI=1S/C32H27N5O5S/c1-19(38)41-17-23-18-43-30-26(36-32-34-24-13-12-20(14-15-33)16-25(24)35-32)29(39)37(30)27(23)31(40)42-28(21-8-4-2-5-9-21)22-10-6-3-7-11-22/h2-13,16,26,28,30H,14,17-18H2,1H3,(H2,34,35,36)/t26-,30?/m1/s1

Standard InChI Key:  LEDUAFDOPWZJFV-FIQOPJFZSA-N

Alternative Forms

1. Parent:

   

   ALA13554

   benzhydryl (7R)-3-(acetyloxymethyl)-7-[[6-(cyanomethyl)-1H-benzimidazol-2-yl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 593.67

Molecular Weight (Monoisotopic): 593.1733

AlogP: 4.47

#Rotatable Bonds: 9

Polar Surface Area: 137.41

Molecular Species: NEUTRAL

HBA: 9

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 10

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 11.89

CX Basic pKa: 6.82

CX LogP: 4.08

CX LogD: 3.98

Aromatic Rings: 4

Heavy Atoms: 43

QED Weighted: 0.21

Np Likeness Score: -0.27

References

1. Jung F, Delvare C, Boucherot D, Hamon A, Ackerley N, Betts MJ..  (1991)  Synthesis and structure-activity relationship of new cephalosporins with amino heterocycles at C-7. Dependence of the antibacterial spectrum and beta-lactamase stability on the pKa of the C-7 heterocycle.,  34  (3): [PMID:2002452] [10.1021/jm00107a035]

Source

Source(1):

• Scientific Literature